Pyridone dyes containing a oxydiazone substituent

Abstract

Compounds of the general formula I ##STR1## where R is hydrogen or an aliphatic, alkenyl, cycloaliphatic, araliphatic, aromatic or heteroaromatic radical, R.sup.1 is hydrogen, amino, hydroxyl or C.sub.1 -C.sub.3 -alkyl, R.sup.2 is hydrogen, unsubstituted or substituted alkyl, allyl, aralkyl or aryl or alkylamino or arylamino, X is hydrogen, chlorine, bromine, nitro, methyl, phenoxy, tolyloxy, dimethylphenoxy, chlorophenoxy or C.sub.1 -C.sub.8 -alkoxy, Y is hydrogen, chlorine or bromine, and Z is hydrogen, acetyl, carbamyl or cyano, are useful for dyeing and/or printing textile material.

Description

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to compounds of the general formula I ##STR2## where R is hydrogen or an aliphatic, alkenyl, cycloaliphatic, araliphatic, aromatic or heteroaromatic radical, R.sup.1 is hydrogen, amino, hydroxyl or C.sub.1 -C.sub.3 -alkyl, R.sup.2 is hydrogen, unsubstituted or substituted alkyl, allyl, aralkyl or aryl or alkylamino or arylamino, X is hydrogen, chlorine, bromine, nitro, methyl, phenoxy, tolyloxy, dimethylphenoxy, chlorophenoxy or C.sub.1 -C.sub.8 -alkoxy, Y is hydrogen, chlorine or bromine, and Z is hydrogen, acetyl, carbamyl or cyano.

2. Description of the Prior Art:

R is, for example, C.sub.1 -C.sub.17 -alkyl which can furthermore be interrupted by oxygen and substituted by, for example, phenyl, methylphenyl, carboxyl, a carboxylic ester group or unsubstituted or substituted phenoxy, or R is hydroxycarbonylvinyl, alkoxycarbonylvinyl, cycloalkyl of 5 to 7 carbon atoms, phenyl which is unsubstituted or substituted by chlorine, bromine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or pyridyl or thienyl.

Specific examples of radicals R are methyl, ethyl, n- and i-propyl, n- and i-butyl, n- and i-pentyl, n-hexyl, n-heptyl, 1-ethylpentyl, decyl, undecyl, dodecyl, C.sub.15 H.sub.31, C.sub.17 H.sub.35, H.sub.5 C.sub.2 O.sub.2 CC.sub.2 H.sub.4 --, H.sub.9 C.sub.4 O.sub.2 CC.sub.2 H.sub.4 --, ##STR3## H.sub.3 COC.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, H.sub.5 C.sub.2 OC.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, H.sub.9 C.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, 2-ethylhexyloxymethyl and -ethyl, hexyloxyethyl, isopropoxyethyl, phenyl, chlorophenyl, cyclohexyl and in particular phenoxymethyl and -ethyl and benzyloxymethyl.

Alkyl radicals R.sup.2 are in particular, of not more than 18 carbon atoms, and can be straight-chain or branched. Phenyl-C.sub.1 -C.sub.4 -alkyl and unsubstituted or substituted phenyl or phenylamino are also suitable.

Specific examples of radicals R.sup.2 are methyl, ethyl, n- and i-propyl, n- and i-butyl, n-pentyl, n-hexyl, n- and i-heptyl, n- and i-octyl, n-nonyl, n-decyl, n-undecyl, phenyl, m-tolyl, p-tolyl, phenylamino, 2-ethylhexyloxypropyl, hexyloxypropyl, hydroxyethoxyethyl and hydroxybutoxypropyl.

Examples of alkoxy radicals X are octyloxy, .beta.-ethylhexyloxy, hexyloxy, phenoxy, amyloxy, butoxy, i-butoxy, propoxy, i-propoxy, ethoxy and, preferably, methoxy.

To prepare the compounds of the formula I, a diazonium compound of an amine of the formula ##STR4## can be reacted with a coupling component of the formula ##STR5## In the Examples which follow, and illustrate the preparation, parts and percentages are by weight, unless stated otherwise.

Of particular importance are compounds of the formula Ia ##STR6## where R is C.sub.3 -C.sub.17 -alkyl, or is C.sub.1 - or C.sub.2 -alkyl which is substituted by C.sub.4 -C.sub.8 -alkoxy, phenoxy or benzyloxy, or is C.sub.1 -C.sub.4 alkyl which is substituted by C.sub.1 -C.sub.8 -alkoxycarbonyl which may or may not be interrupted by oxygen, and R.sup.2 is hydrogen, C.sub.1 -C.sub.6 -alkyl or allyl, and R.sup.2 is not hydrogen when R contains a phenyl ring. Preferably the sum of the carbon atoms of R and R.sup.2 together is from 4 to 13, in particular from 5 to 11.

If R.sup.2 is hydrogen, R should preferably not contain a phenyl ring.

The compounds of the formula I are yellow disperse dyes which have very good fastness properties and excellent color strength. Moreover, the tinctorial properties are generally satisfactory.

Dyes which contain hydroxyl groups in R or R.sup.2 are, as a rule, suitable for leather and nylon.

Some of the dyes are also useful for printing on cotton and cotton/polyester blends, for example by the method described in German Patent No. 1,811,796.

The stated .lambda..sub.max values for the dyes were determined in a solution comprising 9 parts of dimethylformamide and 1 part of glacial acetic acid.

EXAMPLES 1

98 parts of the compound of the formula ##STR7## are dissolved in 250 parts by volume of 96-98% strength sulfuric acid at from 0.degree. to 20.degree. C., 25 parts by volume of a 98% strength nitric acid are added at from 10.degree. to 40.degree. C., while cooling, the mixture is stirred overnight at room temperature and then poured onto about 900 parts of ice and 300 parts of water at 0.degree. C., and stirring is then continued to complete the reaction. The resulting precipitate of the product of the formula ##STR8## is filtered off under suction, washed neutral with water, and dried to give 116 parts of a colorless powder having a melting point of 110.degree. C.

210 parts of this product in 500 parts by volume of alcohol and 900 parts by volume of 25% strength ammonia water are stirred in an autoclave for 10 hours at 150.degree. C.

Thereafter, the solvent is distilled off as far as possible, and water is added to the residue to precipitate the product. The latter is filtered off under suction and dried, and 193 parts of the diazo component of the formula ##STR9## are obtained. 44 parts of this diazo component are stirred with 210 parts by volume of glacial acetic acid, about 60 parts of bromine are then added dropwise at from 25.degree. to 55.degree. C., and at the same time about 80 parts of sodium acetate are added.

After the bromination, the mixture is poured into water, and the pH is brought to 4-6 with sodium hydroxide solution. The product is filtered off under suction, washed with water and dried to give 56 parts of a yellow powder of the formula ##STR10## which has a melting point of 152.degree. C.

13.5 parts of the bromine-free product are suspended in 80 parts by volume of glacial acetic acid, 20 parts by volume of propionic acid and 3 parts of sulfuric acid, 22 parts of a 44% strength solution of nitrosylsulfuric acid are added dropwise in the course of 20 minutes at from 0.degree. to 7.degree. C., and the mixture is then stirred for a further 2-3 hours at from 0.degree. to 5.degree. C. The clear solution is then poured onto about 180 parts of ice and 150 parts of water at 0.degree. C., and excess nitrous acid is destroyed in a conventional manner. The pH of the solution is then increased to 1.0-1.5 by adding a little sodium acetate, the temperature being kept at 0.degree. C. by adding ice.

A solution of 14.5 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one in 200 parts of water and 10 parts of 50% strength sodium hydroxide solution are run into the resulting diazonium salt solution, while stirring thoroughly, the temperature being kept at 0.degree.-10.degree. C. by adding ice water. A yellow precipitate of the dye of the formula ##STR11## is obtained.

Filtration under suction, washing with water and drying in a conventional manner give 24.4 parts of a yellow powder which dissolves in dimethylformamide to give a yellow solution. The dye dyes polyester fabric in very lightfast intense hues, and has very good tinctorial properties. A solution of the dye in a 9:1 mixture of acetonitrile with glacial acetic acid has an absorption maximum at 442 nm (concentration about 0.01 part/1,000 parts by volume).

For example, the intermediates of the general formula II which are listed in Table A can be prepared by a procedure similar to that described in Example 1.

TABLE A______________________________________ ##STR12## II .lambda..sub.max .multidot. Melting (mm,in pointNo. R X Y Z CH.sub.3 OH) .degree.C.______________________________________ 1 CH.sub.3 H Cl Cl 108 2 CH.sub.3 NO.sub.2 Cl Cl 93 3 CH.sub.3 NO.sub.2 Br NH.sub.2 150-153 4 CH.sub.3 NO.sub.2 Cl NH.sub.2 95-97 5 C.sub.2 H.sub.5 NO.sub.2 H NH.sub.2 123-125 6 C.sub.2 H.sub.5 NO.sub.2 Cl NH.sub.2 402 7 C.sub.2 H.sub.5 NO.sub.2 Br NH.sub.2 127-129 8 C.sub.2 H.sub.5 H H Cl 16-20 9 C.sub.2 H.sub.5 NO.sub.2 H Cl 45-4910 C.sub. 3 H.sub.7 H H Cl 57-5811 C.sub.3 H.sub.7 NO.sub.2 H Cl 36-4012 C.sub.3 H.sub.7 NO.sub.2 H NH.sub.2 128-13113 C.sub.3 H.sub.7 NO.sub.2 Cl NH.sub.2 40314 C.sub.3 H.sub.7 NO.sub.2 Br NH.sub.2 85-8715 (CH.sub.3).sub.2 CH H H Cl <2516 (CH.sub.3).sub.2 CH NO.sub.2 H Cl 30-3317 (CH.sub.3).sub.2 CH NO.sub.2 Cl NH.sub.2 40318 (CH.sub.3).sub.2 CH NO.sub.2 Br NH.sub.2 40319 ##STR13## H H Cl 10-2020 ##STR14## NO.sub.2 H Cl 304 20-2621 ##STR15## NO.sub.2 H NH.sub.2 60-6622 ##STR16## NO.sub.2 Cl NH.sub.2 403.523 ##STR17## NO.sub.2 Br NH.sub.2 403.524 n-C.sub.5 H.sub.11 H H Cl 24625 n-C.sub.5 H.sub.11 NO.sub.2 H Cl 30626 n-C.sub.5 H.sub.11 NO.sub.2 H NH.sub.2 40527 n-C.sub.5 H.sub.11 NO.sub.2 Cl NH.sub.2 40328 n-C.sub.5 H.sub.11 NO.sub.2 Br NH.sub.2 40329 (CH.sub.3).sub.3 C H H Cl 246.5 0-530 (CH.sub.3).sub.3 C NO.sub.2 H Cl 303 10331 (CH.sub.3).sub.3 C NO.sub.2 H NH.sub.2 406.5 133-13532 (CH.sub.3).sub.3 C NO.sub.2 Cl NH.sub.2 134-13633 (CH.sub.3).sub.3 C NO.sub.2 Br NH.sub.2 402.5 135-13734 n-C.sub.6 H.sub.13 H H Cl 24635 n-C.sub.6 H.sub.13 NO.sub.2 H Cl 30736 n-C.sub.6 H.sub.13 NO.sub.2 H NH.sub.2 40737 n-C.sub.6 H.sub.13 NO.sub.2 Cl NH.sub.2 404.538 n-C.sub.6 H.sub.13 NO.sub.2 Br NH.sub.2 404.539 CH.sub.3 OCH.sub.2 CH.sub.2 NO.sub.2 H NH.sub.2 137-14140 CH.sub.3 OCH.sub.2 CH.sub.2 NO.sub.2 Br NH.sub.2 401.541 n-C.sub.7 H.sub.15 H H Cl 24742 n-C.sub.7 H.sub.15 NO.sub.2 H Cl 30543 n-C.sub.7 H.sub.15 NO.sub.2 H NH.sub.2 40744 n-C.sub.7 H.sub.15 NO.sub.2 Cl NH.sub.2 40645 n-C.sub.7 H.sub.15 NO.sub.2 Br NH.sub.2 40646 ##STR18## H H Cl <1047 ##STR19## NO.sub.2 H Cl 304 .ltoreq.1648 ##STR20## NO.sub.2 H NH.sub.2 405.549 ##STR21## NO.sub.2 Cl NH.sub.2 40450 ##STR22## NO.sub.2 Br NH.sub.2 40551 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H H Cl 24552 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 NO.sub.2 H Cl 30753 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 NO.sub.2 H NH.sub.2 40554 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 NO.sub.2 Cl NH.sub.2 40655 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 NO.sub.2 Br NH.sub.2 40656 CH.sub.3 (CH.sub.2).sub.10 H H Cl 24657 CH.sub.3 (CH.sub.2).sub.10 NO.sub.2 H Cl 30658 CH.sub.3 (CH.sub.2).sub.10 NO.sub.2 H NH.sub.2 40759 CH.sub.3 (CH.sub.2).sub.10 NO.sub.2 Cl NH.sub.2 40660 CH.sub.3 (CH.sub.2).sub.10 NO.sub.2 Br NH.sub.2 40661 CH.sub.3 (CH.sub.2).sub.14 H H Cl 24762 CH.sub.3 (CH.sub.2).sub.14 NO.sub.2 H Cl 30663 CH.sub.3 (CH.sub.2).sub.14 NO.sub.2 H NH.sub.2 40764 CH.sub.3 (CH.sub.2).sub.14 NO.sub.2 Cl NH.sub.2 40665 CH.sub.3 (CH.sub.2).sub.14 NO.sub.2 Br NH.sub.2 40666 CH.sub.3 (CH.sub.2).sub.16 H H Cl 24767 CH.sub.3 (CH.sub.2).sub.16 NO.sub.2 H Cl 30768 CH.sub.3 (CH.sub.2).sub.16 NO.sub.2 H NH.sub.2 40769 CH.sub.3 (CH.sub.2).sub.16 NO.sub.2 Cl NH.sub.2 40670 CH.sub.3 (CH.sub.2).sub.16 NO.sub.2 Br NH.sub.2 40671 CH.sub.3 OCH.sub.2 H H Cl 66-7072 CH.sub.3 OCH.sub.2 NO.sub.2 H Cl 30373 CH.sub.3 OCH.sub.2 NO.sub.2 H NH.sub.2 40574 CH.sub.3 OCH.sub.2 NO.sub.2 Cl NH.sub.2 40175 CH.sub.3 OCH.sub.2 NO.sub.2 Br H 40176 C.sub.2 H.sub.5 OCH.sub.2 H H Cl 64-6777 C.sub.2 H.sub.5 OCH.sub.2 NO.sub.2 H Cl 30378 C.sub.2 H.sub.5 OCH.sub.2 NO.sub.2 H NH.sub.2 40679 C.sub.2 H.sub.5 OCH.sub.2 NO.sub.2 Cl NH.sub.2 40180 C.sub.2 H.sub.5 OCH.sub.2 NO.sub.2 Br NH.sub.2 40181 C.sub.3 H.sub.7OCH.sub.2 H H Cl 33-3882 C.sub.6 H.sub.5 H H Cl 11583 C.sub.6 H.sub.5 NO.sub.2 H Cl 245.5______________________________________

EXAMPLE 2

240 parts of 3-acetylaminobenzonitrile in a mixture of 450 parts by volume of water, 87 parts of sodium carbonate, 129 parts of hydroxylamine sulfate and 450 parts by volume of isobutanol, and 2 parts of a compound which forms a complex with heavy metals (eg. ethylenediaminetetraacetic acid), are stirred for 6 hours, with vapor cooling, after which the lower, aqueous phase is cooled and then separated off, and 450 parts by volume of distilled water are added. 270 parts of 2-ethylhexanoyl chloride and sodium carbonate are then added, while stirring very thoroughly, so that the mixture is kept at pH 4-7, and stirring is then continued for a further 30 minutes. The mixture is then diluted with water, and the resulting precipitate is filtered off under suction, washed with water and dried to give 420 parts of the compound of the formula ##STR23## of melting point 148.degree. C.

If the product obtained is heated at 150.degree.-160.degree. C., and the melt is stirred for 1 hour at this temperature, water is eliminated to give the compound of the formula ##STR24## in the form of a viscous oil which, after standing for a relatively long time, crystallizes to give a product of melting point 88.degree.-90.degree. C. Yield: 380 parts.

75 parts of this oil in 250 parts by volume of methanol are stirred with 50 parts of concentrated sulfuric acid for from 2 to 21/2 hours, with vapor cooling. Thereafter, some of the methanol is distilled off, precipitation is effected by pouring the mixture onto ice water, and the pH is increased to 5-7. The oily phase is extracted with cyclohexane, ethyl acetate, etc., and the product of the formula ##STR25## is isolated in a conventional manner.

64 parts of a very slightly yellowish oil, whose UV spectrum in methanol has a maximum at 318 nm, are obtained.

For example, the intermediates of the formula III which are shown in Table B can be obtained by a procedure similar to that described in Examples 1 and 2.

TABLE B__________________________________________________________________________ ##STR26## III .lambda..sub.max (nm) or meltingNo. R X Z point (.degree.C.)__________________________________________________________________________1 CH.sub.3 H NHCOCH.sub.3 170-1732 CH.sub.3 NHCOCH.sub.3 H 90-923 CH.sub.3 Cl Cl 108-1114 C.sub.2 H.sub.5 H NHCOC.sub.2 H.sub.5 148-1505 C.sub.2 H.sub.5 NHCOCH.sub.3 H 1316 C.sub.3 H.sub.7 NHCOCH.sub.3 H 295.5 nm7 C.sub.3 H.sub.7 H NHCOCH.sub.3 1368 HO.sub.2 CC.sub.2 H.sub.4 NHCOCH.sub.3 1549 n-C.sub.4 H.sub.9 NHCOCH.sub.3 NHCOCH.sub.3 276.5 nm10 t-C.sub.4 H.sub.9 NHCOCH.sub.3 NHCOCH.sub.3 170-17211 CH.sub.2 OC.sub.6 H.sub.5 NHCOCH.sub.3 H 108-11012 n-C.sub.4 H.sub.9 NHCOCH.sub.3 H 156-16013 n-C.sub.6 H.sub.13 H NHCHO 153-15714 n-C.sub.6 H.sub.13 H NHCOCH.sub.3 272 nm15 ##STR27## H NHCOCH.sub.3 158-16316 n-C.sub.7 H.sub.15 NHCOCH.sub.3 H 144-14517 n-C.sub.8 H.sub.17 NHCOCH.sub.3 H 141-14418 n-C.sub.8 H.sub.17 H NHCOCH.sub.3 274 nm19 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 NHCOCH.sub.3 H 135-14020 n-C.sub.11 H.sub.23 NHCOCH.sub.3 H 237-24121 n-C.sub.11 H.sub.23 H NHCOCH.sub.3 273 nm22 CH.sub.3 (CH.sub.2).sub.12 H NHCOCH.sub.3 272.5 nm23 CH.sub.3 (CH.sub.2).sub.12 NHCOCH.sub.3 H 295.5 nm24 CH.sub.3 (CH.sub.2).sub.14 NHCOCH.sub.3 H 296 nm25 CH.sub.3 (CH.sub.2).sub.14 H NHCOCH.sub.3 136-13926 CH.sub.3 (CH.sub.2).sub.16 H NHCOCH.sub.3 12727 CH.sub.3 OCH.sub.2 H NHCOCH.sub.3 129-13028 CH.sub.3 OCH.sub.2 NHCOCH.sub.3 H 294 nm29 C.sub. 2 H.sub.5 OCH.sub.2 NHCOCH.sub.3 H 156-16030 C.sub.2 H.sub.5 OCH.sub.2 H NHCOCH.sub.3 276 nm31 (CH.sub.3).sub.2 CH H NHCOCH.sub.3 271 nm32 (CH.sub.3).sub.2 CH NHCOCH.sub.3 H 295 nm33 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.2 H NHCOCH.sub.3 15034 C.sub.6 H.sub.5 H NHCOCH.sub.3 183-18535 ClCH.sub.2 CH.sub.2 H NHCOCH.sub.3 163 (decomposition)36 CH.sub.3 Cl Cl 11137 ##STR28## H NHCOCH.sub.3 12038 CH.sub.2CH H NHCOCH.sub.3 160-162 (decomposition)39 ClCH.sub.2 H NHCOCH.sub.3 185-188 (decomposition)40 ##STR29## H NHCOCH.sub.3 220-23041 HO.sub.2 CCH.sub.2 CH.sub.2 H NHCOCH.sub.3 270 nm (154)42 HO.sub.2 CCH CH H NHCOCH.sub.3 278 nm43 ClCH.sub.2 CH.sub.2 CH.sub.2 H NHCOCH.sub.3 273 nm44 C.sub.6 H.sub.5 OCH.sub.2 H NHCOCH.sub.3 155__________________________________________________________________________

EXAMPLE 3

144 parts of 4-acetylaminobenzamidoxime are dissolved in 200 parts by volume of N-methylpyrrolidone and 200 parts by volume of acetone, and 90 parts of volume of butyryl chloride are added, 10% strength sodium hydroxide solution being added at the same time so that the pH of the reaction mixture is kept at 4.5-7.0. Stirring is continued for 1 hour at from 25.degree. to 45.degree. C., after which precipitation is effected by dilution with water, and the precipitate is filtered off under suction, washed salt-free with water and dried to give 180 parts of the product of the formula ##STR30##

When the colorless powder is heated at 170.degree. C., water is eliminated to give the product of the formula ##STR31## in the form of a melt which, when it is cooled, solidifies to give a product of melting point 171.degree. C.

This compound is brominated by a conventional method (for example in glacial acetic acid or sulfuric acid at .ltoreq.40.degree. C.) to give 1-acetylamino-2-bromo-4-(5-n-propyl-1,2,4-oxadiazol-3-yl)-benzene of the formula ##STR32## (UV spectrum: .lambda..sub.max =268.5 nm in methanol).

41 parts of this product in 200 parts by volume of methanol are stirred with 30 parts of concentrated sulfuric acid, with vapor cooling. After 1 hour, the mixture is neutralized and some of the methanol is then distilled off. The reaction mixture is diluted with water, and the resulting precipitate is filtered off under suction, washed with water and dried to give 33 parts of the diazo component of the formula ##STR33## in the form of a colorless powder of melting point 88.degree.-90.degree. C.

41 parts of 4-(5-n-propyl-1,2,4-oxadiazol-3-yl)aniline in 200 parts by volume of glacial acetic acid and 45 parts of anhydrous sodium acetate are stirred, 80 parts of bromine are added at from 20.degree. to 50.degree. C., stirring is continued for a further 2 hours and the resulting, colorless product of the formula ##STR34## is precipitated with water (.lambda..sub.max =284.5 nm).

The product is filtered off under suction, washed with water and dried to give 69 parts of a colorless powder. If the bromination is carried out in 85-98% sulfuric acid, a smaller amount of bromine is required.

The compounds of the general formula IV which are stated in Table C can be prepared by a procedure similar to that described in the Examples.

TABLE C__________________________________________________________________________ ##STR35## IV .lambda..sub.max. (nm) or meltingNo. R X.sup.1 X Y Z point (.degree.C.)__________________________________________________________________________1 CH.sub.3 H Cl H NHCOCH.sub.3 134-136 (269.0 nm)2 CH.sub.3 H Cl H NH.sub.2 283 nm3 CH.sub.3 H H NH.sub.2 H 97-984 CH.sub.3 H Cl Cl NH.sub.2 110 (282.5 nm)5 CH.sub.3 H Br H NHCOCH.sub.3 152-1556 CH.sub.3 H Br H NH.sub.2 148-150 (284.0 nm)7 CH.sub.3 H Br Br NH.sub.2 160-161 (283 nm)8 CH.sub.3 Br H NH.sub.2 Br 289 nm9 CH.sub.3 NO.sub.2 H NH.sub.2 H 130-13510 CH.sub.3 H H NH.sub.2 NO.sub.2 98-10311 CH.sub.3 H CH.sub.3 H NO.sub.2 143-14512 CH.sub.3 H CH.sub.3 H NH.sub.2 136-13813 CH.sub.3 CH.sub.3 H NH.sub.2 H 322 nm14 C.sub.2 H.sub.5 H H H NHCOCH.sub.3 149-15015 C.sub.2 H.sub.5 H H Br NHCOCH.sub.3 113-114 (268.5 nm)16 C.sub.2 H.sub.5 H H Br NH.sub.2 65-67 (248.5 nm)17 C.sub.2 H.sub.5 H H Cl NH.sub.2 283 nm18 C.sub.2 H.sub.5 H Cl Cl NH.sub.2 290 nm19 C.sub.2 H.sub.5 H H Cl NHCOCH.sub.3 267 nm20 C.sub.2 H.sub.5 H Br Br NH.sub.2 284.5 nm21 C.sub.2 H.sub.5 Br H NHCOCH.sub.3 Br 160-165 (290.5 nm)22 C.sub.2 H.sub.5 H H NH.sub.2 H 318 230 nm23 C.sub.2 H.sub.5 H H NHCOCH.sub.3 H 302 nm24 C.sub.2 H.sub.5 Br H NH.sub.2 Br 306 nm25 C.sub.2 H.sub.5 H H NH.sub.2 NO.sub.2 95-9926 C.sub.2 H.sub.5 NO.sub.2 H NH.sub.2 H 76-8127 n-C.sub.3 H.sub.7 H H H NHCOCH.sub.3 168-17128 n-C.sub.3 H.sub.7 H Cl H NHCOCH.sub.3 267 nm29 n-C.sub.3 H.sub.7 H Cl H NH.sub.2 218 and 283 nm30 n-C.sub.3 H.sub.7 H Cl Cl NH.sub.2 283 nm31 n-C.sub.3 H.sub.7 H H NHCOCH.sub.3 H 299 nm32 n-C.sub.3 H.sub.7 H H NH.sub.2 H 317 and 229 nm33 n-C.sub.3 H.sub.7 H H H NH.sub.2 88-9034 CH.sub.3 OCH.sub.2 H H NHCOCH.sub.3 H 302 nm35 CH.sub.3 OCH.sub.2 H Br H NHCOCH.sub.3 79-8336 CH.sub.3 OCH.sub.2 H Br H H 269 nm37 CH.sub.3 OCH.sub.2 H H NH.sub.2 H 316 nm38 CH.sub.3 OCH.sub.2 H Br Br NH.sub.2 283 nm39 CH.sub.3 OCH.sub.2 H Cl Cl NH.sub.2 282 nm40 CH.sub.3 OCH.sub.2 H H Cl NH.sub.2 218 and 282 nm41 CH.sub.3 OCH.sub.2 H H Br NH.sub.2 46-49 286.5 nm42 CH.sub.3 OCH.sub.2 H H H NHCHO 276 nm43 CH.sub.3 OCH.sub.2 H H NHCHO H 308 nm44 (CH.sub.3).sub.3 C H Br H NH.sub.2 56-58 284.5 nm45 (CH.sub.3).sub.3 C H Br Br NH.sub.2 87-89 284.5 nm46 CH.sub.3 OCH.sub.2 CH.sub.2 H H NHCOCH.sub.3 H 294 nm47 CH.sub.3 OCH.sub.2 CH.sub.2 H H H NHCOCH.sub.3 273 nm48 CH.sub.3 OCH.sub.2 CH.sub.2 H Br H NHCOCH.sub.3 268 nm49 CH.sub.3 OCH.sub.2 CH.sub.2 H Br Br NHCOCH.sub.3 275 nm50 (CH.sub.3).sub.2 CH H H NHCOCH.sub.3 H 296 nm51 (CH.sub.3).sub.2 CH H H H NHCOCH.sub.3 275 nm52 (CH.sub.3).sub.2 CH H H Br NHCOCH.sub.3 267.5 nm53 (CH.sub.3).sub.2 CH H H Br NH.sub.2 220 and 285 nm54 (CH.sub.3).sub.2 CH H H NH.sub.2 H 228 and 318 nm55 (CH.sub.3).sub.2 CH H Br Br NH.sub.2 222 and 285 nm56 (CH.sub.3).sub.2 CH H Cl Cl NH.sub.2 221 and 283 nm57 (CH.sub.3).sub.2 CH H Cl H NH.sub.2 286 nm58 n-C.sub.4 H.sub.9 H H NHCOCH.sub.3 H 296 nm59 n-C.sub.4 H.sub.9 H H H NHCOCH.sub.3 274 nm60 n-C.sub.4 H.sub.9 H H H NH.sub.2 286 nm61 n-C.sub.4 H.sub.9 H H Br NH.sub.2 288 nm62 n-C.sub.4 H.sub.9 H Br Br NH.sub.2 222 and 284.5 nm63 n-C.sub.4 H.sub.9 H Cl Cl NH.sub.2 221 and 284 nm64 (CH.sub.3).sub.3 C H H NHCOCH.sub.3 H 295 nm65 (CH.sub.3).sub.3 C H H H NHCOCH.sub.3 173-17566 (CH.sub.3).sub.3 C H H Br NHCOCH.sub.3 85-8767 (CH.sub.3).sub.3 C H H Cl NHCOCH.sub.3 220 and 268 nm68 n-C.sub.6 H.sub.13 H H NHCOCH.sub.3 H 231.5 and 296 nm69 n-C.sub.6 H.sub.13 H H NH.sub.2 H 228.5 and 316 nm70 n-C.sub.6 H.sub.13 H H H NHCOCH.sub.3 273 nm71 n-C.sub.6 H.sub.13 H H H NH.sub.2 284 nm72 n-C.sub.6 H.sub.13 H H Br NH.sub.2 286 nm73 n-C.sub.6 H.sub.13 H H Br NHCOCH.sub.3 287 nm74 n-C.sub.6 H.sub.13 H H Cl NHCOCH.sub.3 268 nm75 n-C.sub.6 H.sub.13 H Br Br NH.sub.2 285 nm76 n-C.sub.6 H.sub.13 H Cl Cl NH.sub.2 284 nm77 n-C.sub.7 H.sub.15 H Cl Cl NH.sub.2 285 nm78 n-C.sub.7 H.sub.15 H H Cl NHCOCH.sub.3 268.5 nm79 n-C.sub.7 H.sub.15 H H H NHCOCH.sub.3 274 nm80 n-C.sub.7 H.sub.15 H H Br NHCOCH.sub.3 276 nm81 n-C.sub.7 H.sub.15 H H Br NH.sub.2 284.5 and 220 nm82 n-C.sub.7 H.sub.15 H Br Br NH.sub.2 285 nm83 n-C.sub.7 H.sub.15 H H NH.sub.2 H 316.5 and 228 nm84 n-C.sub.7 H.sub.15 H H NHCOCH.sub.3 H 295 and 231 nm85 n-C.sub.7 H.sub.15 H H Cl NH.sub.2 285 nm86 n-C.sub.7 H.sub.15 H H NH.sub.2 Cl 320 nm87 ##STR36## H Br Br NH.sub.2 285 nm88 ##STR37## H H Br NH.sub.2 284 nm89 ##STR38## H H Cl NHCOCH.sub.3 2590 ##STR39## H H Br NHCOCH.sub.3 2591 ##STR40## H H Br NH.sub.2 2092 ##STR41## H H H NHCOC.sub.2 H.sub.5 48-5393 ##STR42## H H NH.sub.2 Cl 10-1694 ##STR43## H H H NH.sub.2 38-4095 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H H H H 317 and 228 nm96 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H H NHCOCH.sub.3 H 296 nm97 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H H H NHCOCH.sub.3 269 nm98 (CH.sub. 3).sub.3 C(CH.sub.2).sub.5 H H Br NHCOCH.sub.3 268.5 nm99 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H H Br NH.sub.2 287 nm100 (CH.sub.3).sub.3 C(CH.sub.2).sub.5 H Br Br NH.sub.2 285 nm101 CH.sub.3 (CH.sub.2).sub.10 H Br Br NH.sub.2 286 nm102 CH.sub.3 (CH.sub.2).sub.10 H H Br NH.sub.2 287 nm103 CH.sub.3 (CH.sub.2).sub.10 H H H NH.sub.2 285 nm104 CH.sub.3 (CH.sub.2).sub.10 H H H NHCOCH.sub.3 296 nm105 CH.sub.3 (CH.sub.2).sub.10 H H Br NHCOCH.sub.3 269 nm106 CH.sub.3 (CH.sub.2).sub.10 H Br Br NH.sub.2 286 nm107 CH.sub.3 (CH.sub.2).sub.10 H H NHCOCH.sub.3 H 296.5 nm108 CH.sub.3 (CH.sub.2).sub.10 H H NH.sub.2 H 319 nm109 CH.sub.3 (CH.sub.2).sub.14 H H NH.sub.2 H110 CH.sub.3 (CH.sub.2).sub.14 H H H NHCOCH.sub.3 78-85111 CH.sub.3 (CH.sub.2).sub.14 H H H NH.sub.2 285.5 nm 50-60112 CH.sub.3 (CH.sub.2).sub.14 H H Br NH.sub.2 286 nm113 CH.sub.3 (CH.sub.2).sub.14 H Br Br NH.sub.2 287 nm114 CH.sub.3 (CH.sub.2).sub.14 H H Br NHCOCH.sub.3 270 nm115 CH.sub.3 (CH.sub.2).sub.14 H H NH.sub.2 H 320 nm116 C.sub.17 H.sub.35 H H H NHCOCH.sub.3 80-85117 CH.sub.3 (CH.sub.2).sub.16 H H NH.sub.2 H 319 nm118 CH.sub.3 (CH.sub.2).sub.16 H H H NH.sub.2 286 nm119 CH.sub.3 (CH.sub.2).sub.16 H H Br NH.sub.2 287 nm120 CH.sub.3 (CH.sub.2).sub.16 H Br Br NH.sub.2 288 nm121 CH.sub.3 (CH.sub.2).sub.16 H H Br NHCOCH.sub.3 274 nm122 ##STR44## H H H NHCOCH.sub.3 250-253123 C.sub.6 H.sub.5 H H H NHCOCH.sub.3 180-183123a C.sub.6 H.sub.5 H H NHCOCH.sub.3 H 190-193124 C.sub.6 H.sub.5 H H Br NHCOCH.sub.3 268.5 nm125 C.sub.6 H.sub.5 H Br Br NHCOCH.sub.3 269 nm126 C.sub.6 H.sub.5 H Cl Cl NHCOCH.sub.3 266 nm127 C.sub.6 H.sub.5 H Cl Cl NH.sub.2 142-145128 C.sub.6 H.sub.5 H H Br NH.sub.2 289 nm129 C.sub.6 H.sub.5 H H Cl NH.sub.2 289 nm130 C.sub.6 H.sub.5 H H NH.sub.2 H 320 nm 143-145131 ##STR45## H H NH.sub.2 H 317 nm132 ##STR46## H H H NH.sub.2 287 nm133 ##STR47## H H H NHCOCH.sub.3 275 nm134 ##STR48## H H Br NHCOCH.sub.3 268 nm135 C.sub.6 H.sub.5 OCH.sub.2 H H H NHCOCH.sub.3 165 275.0 nm135a C.sub.6 H.sub.5 OCH.sub.2 H NH.sub.2 H H 115136 C.sub.6 H.sub.5 OCH.sub.2 H H H NH.sub.2 110-112137 C.sub.6 H.sub.5 CH.sub.2 OCH.sub.2 H H H NH.sub.2 90-94138 C.sub.6 H.sub.5 CH.sub.2 OCH.sub.2 H H NH.sub.2 H 318 nm139 ##STR49## H H NH.sub.2 H 319 nm140 ##STR50## H H H NH.sub.2 286 nm141 ##STR51## H H NHCOCH.sub.3 H 295 nm142 ##STR52## H H NH.sub.2 H 317 nm143 ##STR53## H H H NH.sub.2 283 nm144 ##STR54## H H H NHCOCH.sub.3 274 nm145 ##STR55## H H Br NHCOCH.sub.3 267 nm146 ##STR56## H H Br NH.sub.2 284 nm147 ##STR57## H H Br NH.sub.2 269 nm148 ##STR58## H H NH.sub.2 H 316 nm149 ##STR59## H H NH.sub.2 H 318 nm150 ##STR60## H H H NH.sub.2 284.5 nm151 ##STR61## H H Br NH.sub.2 289 nm152 C.sub.6 H.sub.5 CH.sub.2 H H H NH.sub.2 285 nm153 C.sub.6 H.sub.5 CH.sub.2 H H NH.sub.2 H 319 nm154 ##STR62## H H NH.sub.2 H 319 and 228 nm155 ##STR63## H H H NH.sub.2 281 nm156 ##STR64## H H H NH.sub.2 103- 105 279.5 nm157 ##STR65## H H H NHCOCH.sub.3 183-185 273.5 nm158 ##STR66## H H NH.sub.2 H 319 and 228 nm159 CH.sub.3 H H NH.sub.2 OCH.sub.3 325 nm160 ##STR67## H H NH.sub.2 OCH.sub.3 325 nm161 CH.sub.3 O.sub.2 CC.sub.2 H.sub.4 H H H NH.sub.2 105-107162 HO.sub.2 CC.sub.2 H.sub.4 H H NH.sub.2 H 318 nm163 HO.sub.2 CC.sub.2 H.sub.4 H H H NH.sub.2 284 nm164 HO.sub.2 CC.sub.2 H.sub.4 H H NH.sub.2 Br 321 nm165 HO.sub.2 CC.sub.2 H.sub.4 H H NHCOCH.sub.3 H 295.5 nm__________________________________________________________________________

EXAMPLE 4

370 parts of the compound of the formula ##STR68## are introduced into 800 g of 96% strength sulfuric acid at from 15.degree. to 20.degree. C., 150 parts by volume of concentrated nitric acid are then added dropwise at from 0.degree. to 10.degree. C., and the mixture is stirred for a further hour at room temperature. When nitration is complete, the mixture is poured onto ice water and stirred until the reaction is complete, and the precipitate is buffered at pH 4.5-7.

The oily phase is separated off, and stirred with about 1,000 parts by volume of methanol. The resulting yellow precipitate is filtered off under suction, washed with methanol and dried to give 100 parts of a product of melting point 143.degree.-146.degree. C., the formula of which is probably ##STR69##

The filtrate contains, in addition to a small amount of this product, an isomer which presumably has the following formula ##STR70## This compound is isolated by evaporating the methanol.

By means of catalytic (or Bechamp) reduction, the nitro compounds are converted to the amines of the formula ##STR71## of melting point 136.degree.-138.degree. C. (or ##STR72## having a melting range from 100.degree. to 135.degree. C., since this product contains a small amount of impurities).

If nitration is carried out using the oxadiazole derivatives of the formulae ##STR73## pure nitro derivatives of the formulae ##STR74## respectively, are obtained, which can be reduced to the corresponding amines in a conventional manner.

The yellow dyes of the general formulae V and VI shown in Tables D and E can be prepared by methods similar to those described.

TABLE D______________________________________ ##STR75## V .lambda..sub.max.No. R R.sup.1 X X.sup.1 Y (nm)______________________________________ ##STR76## CH.sub.3 H H H 4382 ##STR77## C.sub.2 H.sub.5 H H H 439.53 ##STR78## n-C.sub.3 H.sub.7 H H H 439.54 ##STR79## i-C.sub.3 H.sub.7 H H H 439.55 ##STR80## n-C.sub.4 H.sub.9 H H H 439.56 ##STR81## i-C.sub.4 H.sub.9 H H H 439.57 ##STR82## n-C.sub.6 H.sub.13 H H H 439.58 CH.sub.3 (CH.sub.2).sub.6 CH.sub.3 H H H 439.59 CH.sub.3 (CH.sub.2).sub.6 H H H H 43810 CH.sub.3 (CH.sub.2).sub.6 C.sub.2 H.sub.5 H H H 43911 CH.sub.3 (CH.sub.2).sub.6 n-C.sub.3 H.sub.7 H H H 43912 CH.sub.3 (CH.sub.2).sub.6 i-C.sub.3 H.sub.7 H H H 43913 ##STR83## CH.sub.3 H H H 43914 ##STR84## C.sub.2 H.sub.5 H H H 43915 ##STR85## n-C.sub.3 H.sub.7 H H H 43916 ##STR86## i-C.sub.3 H.sub.7 H H H 43917 ##STR87## C.sub.2 H.sub.4 OCH.sub.3 H H H 43918 ##STR88## C.sub.3 H.sub.6 OCH.sub.3 H H H 43919 C.sub.6 H.sub.5 CH.sub.2 OC.sub.2 H.sub.4 CH.sub.3 H H H 439.520 HO.sub.2 CC.sub.2 H.sub.4 H H H H 43821 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 H H H 438.522 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH H H H 438.523 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H H H 438.524 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 H H H 438.525 HO.sub.2 CCH.sub.2 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 H H H 43926 HO.sub.2 CCH.sub.2 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H H H 43927 ##STR89## CH.sub.2 CHCH.sub.2 H H H 439.528 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.3 H H H 43929 C.sub.6 H.sub.5 OCH.sub.2 C.sub.2 H.sub.5 H H H 43930 CH.sub.3 C.sub.2 H.sub.5 H H H 437.531 CH.sub.3 CH.sub.3 H H H 43832 CH.sub.3 H H H H 43833 C.sub.2 H.sub.5 H H H H 43834 C.sub.2 H.sub.5 CH.sub.3 H H H 43835 C.sub.2 H.sub.5 C.sub.2 H.sub.5 H H H 43936 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 H H H 43937 C.sub.2 H.sub.5 CHCH.sub.2CH.sub.2 H H H 44038 n-C.sub.3 H.sub.7 CH.sub.3 H H H 43939 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 H H H 439.540 n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9 H H H 439.541 ##STR90## H Br H H 43842 ##STR91## CH.sub.3 Br H H 43843 ##STR92## CH.sub.3 Cl H H 43844 ##STR93## CH.sub.3 NO.sub.2 H H 44745 ##STR94## H NO.sub.2 H H 44646 ##STR95## C.sub.2 H.sub.5 NO.sub.2 H H 448______________________________________ TABLE E__________________________________________________________________________ ##STR96## VI .lambda..sub.max.(nm) or meltingNo. R R.sup.1 R.sup.2 Y X.sup.1 point (.degree.C.)__________________________________________________________________________1 n-C.sub.3 H.sub.7 CH.sub.3 H NO.sub.2 H 436 nm2 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 H NO.sub.2 H 437 nm3 n-C.sub.3 H.sub.7 n-C.sub.3 H.sub.7 H NO.sub.2 H 437 nm4 n-C.sub.3 H.sub.7 n-C.sub.4 H.sub.9 H NO.sub.2 H 437 nm5 n-C.sub.3 H.sub.7 n-C.sub.6 H.sub.13 H NO.sub.2 H 437 nm6 n-C.sub.7 H.sub.15 H H NO.sub.2 H 110-1167 n-C.sub.7 H.sub.15 CH.sub.3 H NO.sub.2 H 103-1088 n-C.sub.7 H.sub.15 C.sub.2 H.sub.5 H NO.sub.2 H 105-1099 n-C.sub.7 H.sub.15 n-C.sub.3 H.sub.7 H NO.sub.2 H 100-10310 ##STR97## H H NO.sub.2 H 436 nm11 ##STR98## H COCH.sub.3 NO.sub.2 H 439 nm12 ##STR99## CH.sub.3 H NO.sub.2 H 438 nm13 ##STR100## C.sub.2 H.sub.5 H NO.sub.2 H 438 nm14 ##STR101## n-C.sub.3 H.sub.7 H NO.sub.2 H 438 nm15 n-C.sub.8 H.sub.17 H H NO.sub.2 H 437 nm16 n-C.sub.8 H.sub.17 CH.sub.3 H NO.sub.2 H 438 nm17 n-C.sub. 8 H.sub.17 C.sub.2 H.sub.5 H NO.sub.2 H 438 nm18 ##STR102## H CN Br H 429 nm19 ##STR103## H CN Cl Cl 425 nm20 ##STR104## CH.sub.3 CN Cl Cl 426 nm21 ##STR105## CH.sub.3 CN Br H 429 nm22 ##STR106## n-C.sub.4 H.sub.9 CN Cl Cl 425 nm23 ##STR107## n-C.sub.4 H.sub.9 CN Br Br 425 nm24 n-C.sub.8 H.sub.17 CH.sub.2 CH.sub.2 OCH.sub.3 CN H H 428 nm25 n-C.sub.8 H.sub.17 (CH.sub.2).sub.3 OCH.sub.3 CN H H 428 nm26 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4 H CN H H 427.5 nm27 n-C.sub.4 H.sub.9 OC.sub.2 H.sub.4 CH.sub.3 CN Cl H 428 nm28 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4 CH.sub.3 H NO.sub.2 H 436 nm29 n-C.sub.4 H.sub.9OC.sub.2 H.sub.4 C.sub.2 H.sub.5 H NO.sub.2 H 436 nm30 ##STR108## H H NO.sub.2 H 436 nm31 ##STR109## CH.sub.3 H NO.sub.2 H 437 nm32 ##STR110## H CN H H 427.5 nm33 ##STR111## n-C.sub.3 H.sub.7 CN H H 428.5 nm34 ##STR112## C.sub.2 H.sub.5 CN H H 428.5 nm35 ##STR113## C.sub.2 H.sub.5 CN H H 428.5 nm36 ##STR114## CH.sub.3 CN H H 428.5 nm37 ##STR115## CH.sub.3 CN H H 428.5 nm38 ##STR116## CH.sub.3 CN H H 428.5 nm39 HO.sub.2 CC.sub.2 H.sub.4 H CN H H 428.5 nm40 HO.sub.2 CC.sub.2 H.sub.4 H CONH.sub.2 H H 412 nm41 HO.sub.2 CC.sub.2 H.sub.4 H H H H 410 nm42 HO.sub.2 CC.sub.2 H.sub.4 CH.sub.3 H H H 410 nm43 HO.sub.2 CC.sub.2 H.sub.4 CH.sub.3 CONH.sub.2 H H 413 nm44 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 CONH.sub.2 H H 413 nm45 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 H H H 412 nm46 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 CN H H 412 nm47 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH CN H H 429 nm48 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CN H H 429 nm49 ##STR117## H COCH.sub.3 H H 410 nm__________________________________________________________________________

The greenish yellow dyes of the general formula VII which are stated in the Table can be prepared by a procedure similar to that described in the examples.

TABLE F__________________________________________________________________________ ##STR118## VII .lambda..sub.max. (nm) or meltingNo. R R.sup.1 X X.sup.1 point (.degree.C.)__________________________________________________________________________ ##STR119## CH.sub.3 H H 428 nm2 ##STR120## C.sub.2 H.sub.5 H H 428.5 nm3 ##STR121## n-C.sub.3 H.sub.7 H H 428.5 nm4 ##STR122## i-C.sub.3 H.sub.7 H H 428.5 nm5 ##STR123## n-C.sub.4 H.sub.9 H H 429 nm6 ##STR124## i-C.sub.4 H.sub.9 H H 429 nm7 ##STR125## n-C.sub.6 H.sub.13 H H 429 nm8 ##STR126## ##STR127## H H 428 nm9 ##STR128## C.sub.2 H.sub.4 OH H H 428 nm10 ##STR129## C.sub.3 H.sub.6 OH H H 428 nm11 ##STR130## C.sub.6 H.sub.13 OH H H 428 nm12 ##STR131## C.sub.2 H.sub.4 OCH.sub.3 H H 428 nm13 ##STR132## C.sub.3 H.sub.6 OCH H H 428 nm14 ##STR133## C.sub.3 H.sub.6 OC.sub.2 H.sub.5 H H 428 nm15 ##STR134## C.sub.2 H.sub.4 OC.sub.4 H.sub.9 H H 428 nm16 ##STR135## CH.sub.3 Br H 429 nm17 ##STR136## n-C.sub.4 H.sub.9 Br Br 416 nm18 ##STR137## CH.sub.2 CHCH.sub.2 H H 429 nm19 n-C.sub.7 H.sub.15 H H H 427 nm20 n-C.sub.7 H.sub.15 CH.sub.3 H H 427,5 nm 131-13321 n-C.sub.7 H.sub.15 C.sub.2 H.sub.5 H H 427.5 nm 142-14522 n-C.sub.7 H.sub.15 C.sub.3 H.sub.7 H H 427.5 nm23 n-C.sub.6 H.sub.13 H H H 427.5 nm24 n-C.sub.6 H.sub.13 CH.sub.3 H H 427.5 nm25 n-C.sub.6 H.sub.13 C.sub.2 H.sub.5 H H 427.5 nm26 n-C.sub.6 H.sub.13 CH.sub.2 CHCH.sub.2 H H 427.5 nm27 n-C.sub.3 H.sub.7 H H H 427 nm28 n-C.sub.3 H.sub.7 CH.sub.3 H H 427 nm29 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 H H 427 nm30 CH.sub.3 H H H 427 nm31 CH.sub.3 CH.sub.3 H H 427 nm32 CH.sub.3 C.sub.2 H.sub.5 H H 427 nm 228-23133 CH.sub.3 n-C.sub.4 H.sub.9 H H 427 nm34 C.sub.6 H.sub.5 OCH.sub.2 CH(CH.sub.3).sub.2 H H 428 nm35 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.3 H H 428 nm36 C.sub.6 H.sub.5 OCH.sub.2 C.sub.2 H.sub.5 H H 428 nm37 C.sub.6 H.sub.5 OCH.sub.2 n-C.sub.3 H.sub.7 H H 428 nm38 CH.sub.3 OCH.sub.3 n-C.sub.3 H.sub.7 H H 428 nm39 CH.sub.3 OCH.sub.3 C.sub.2 H.sub.5 H H 428 nm40 CH.sub.3 OCH.sub.3 i-C.sub.3 H.sub.7 H H 428 nm41 CH.sub.3 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm42 CH.sub.3 O.sub.2 CC.sub.2 H.sub.4 CH.sub.3 H H 429 nm43 C.sub.2 H.sub.5 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm44 H.sub.9 C.sub.4 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm45 H.sub.13 C.sub.6 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm46 C.sub.4 H.sub.9 O.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm H.sub.3O.sub.247 CACH.sub.2 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 H H 429 nm H.sub.9 C.sub.448 ##STR138## C.sub.2 H.sub.5 H H 430 nm__________________________________________________________________________

EXAMPLE 5

23.5 parts of the diazo component of the formula ##STR139## are diazotized in a conventional manner, and the resulting diazonium salt solution is run into a very thoroughly stirred solution of 24 parts of the coupling component of the formula ##STR140## in 500 parts of water, 200 parts of ice and 10 parts of sodium carbonate.

The coupling mixture is brought to pH 3.5-4.5, and the precipitated dye of the formula ##STR141## is filtered off under suction and isolated in a conventional manner. Drying of the product gives 46 parts of a yellow powder, which dyes nylon fabrics and leather in greenish yellow hues with good fastness properties.

The yellow dyes of the general formula VIII which are shown in Table G can be obtained by a procedure similar to that described in Example 5.

TABLE G__________________________________________________________________________ ##STR142## VIIINo. R R.sup.1 R.sup.2 X H .lambda..sub.max. (nm)__________________________________________________________________________1 n-C.sub.7 H.sub.15 H H NO.sub.2 H 435 nm2 n-C.sub.7 H.sub.15 H COCH.sub.3 NO.sub.2 H 439 nm3 n-C.sub.7 H.sub.15 CH.sub.3 COCH.sub.3 NO.sub.2 H 438 nm4 n-C.sub.7 H.sub.15 CH.sub.3 H NO.sub.2 H 435 nm ##STR143## H H NO.sub.2 H 435 nm6 ##STR144## H COCH.sub.3 NO.sub.2 H 439 nm7 ##STR145## CH.sub.3 COCH.sub.3 NO.sub.2 H 438 nm8 ##STR146## CH.sub.3 H NO.sub.2 H 436 nm9 ##STR147## H CN NO.sub.2 H 446 nm10 ##STR148## CH.sub.3 CN NO.sub.2 H 447 nm11 ##STR149## CH.sub.3 CN Br H 438 nm12 ##STR150## H CN Br H 439 nm13 ##STR151## H CN Cl H 439 nm14 ##STR152## C.sub.2 H.sub.5 H NO.sub.2 H 437 nm15 ##STR153## n-C.sub.4 H.sub.9 H NO.sub.2 H 437 nm16 C.sub.6 H.sub.5 OCH.sub.2 C.sub.2 H.sub.5 CN H H 440 nm17 C.sub.6 H.sub.5 OCH.sub.2 CH.sub.3 CN H H 440 nm18 n-C.sub.11 H.sub.23 C.sub.4 H.sub.9 CN H H 440 nm19 n-C.sub.11 H.sub.23 n-C.sub.6 H.sub.13 CN H H 440 nm20 n-C.sub.11 H.sub.23 C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm21 ##STR154## C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm22 ##STR155## n-C.sub.6 H.sub.13 n-C.sub.6 H.sub.13 H H 440 nm23 ##STR156## C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CN H H 440 nm24 n-C.sub.11 H.sub.23 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CN H H 440 nm25 n-C.sub.15 H.sub.31 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CN H H 440 nm26 n-C.sub.15 H.sub.31 C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm27 n-C.sub.15 H.sub.31 n-C.sub.4 H.sub.9 CN H H 440 nm28 HO.sub.2 CC.sub.2 H.sub.4 H CN H H 440 nm29 HO.sub.2 CC.sub.2 H.sub.4 H CONH.sub.2 H H 426 nm30 HO.sub.2 CC.sub.2 H.sub.4 CH.sub.3 CONH.sub.2 H H 426 nm31 HO.sub.2 CC.sub.2 H.sub.4 CH.sub.3 CN H H 440 nm32 HO.sub.2 CC.sub.2 H.sub.4 CH.sub.3 CONH.sub.2 Br H 428 nm33 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 CONH.sub.2 Br H 428 nm34 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 CONH.sub.2 H H 426 nm35 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.4 OCH.sub.3 CONH.sub.2 H H 426 nm36 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.4 OCH.sub.3 CN H H 440 nm37 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm38 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 CONH.sub.2 H H 426 nm39 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OCH.sub.3 CONH.sub.2 Br H 428 nm40 HO.sub.2 CCHCH H CN H H 440 nm41 HO.sub.2 CCHCH CH.sub.3 CN H H 440 nm42 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.4 OH CN Br H 441 nm43 HO.sub.2 CC.sub.2 H.sub.4 C.sub.3 H.sub.6 OH CN Br H 440 nm44 HO.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CN H H 440 nm45 HO.sub.2 CCHCH C.sub.3 H.sub.6 OH CN H H 440 nm46 HO.sub.2 CCHCH C.sub.2 H.sub.4 OH CN H H 440 nm47 HO.sub.2 CCHCH C.sub.2 H.sub.4 OCH.sub.3 CN H H 440 nm48 HO.sub.2 CCHCH C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm49 HO.sub.2 CCHCH C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CN H H 440 nm50 HO.sub.2 CCH.sub.2 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CN H H 440 nm51 HO.sub.2 CCH.sub.2 C.sub.2 H.sub.4 OH CN H H 440 nm52 HO.sub.2 CCH.sub.2 C.sub.3 H.sub.6 OH CN H H 440 nm53 HO.sub.2 CCHCH C.sub.2 H.sub.4 OCH.sub.3 CONH.sub.2 H H 426 nm54 HO.sub.2 CCHCH C.sub.3 H.sub.6 OCH.sub.3 CONH.sub.2 H H 427 nm55 HO.sub.2 C(CH.sub.2).sub.3 C.sub.3 H.sub.6 OCH.sub.3 CN H H 440 nm56 HO.sub.2 C(CH.sub.2).sub.3 C.sub.2 H.sub.4 OH CN H H 440 nm57 HO.sub.2 C(CH.sub.2).sub.4 C.sub.2 H.sub.4 OH CN H H 440 nm58 HO.sub.2 C(CH.sub.2).sub.4 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CN H H 440 nm59 n-C.sub.3 H.sub.7 CH.sub.3 CN Br Br 416 nm60 ##STR157## H COCH.sub.3 H H 428.5 nm61 ##STR158## H COCH.sub.3 Br H 428.5 nm62 CH.sub.3 O.sub.2 CC.sub.2 H.sub.4 C.sub.2 H.sub.5 CN H H 439 nm__________________________________________________________________________

The dyes stated in Table H can be prepared by a procedure similar to that described in Examples 9, 10 and 11.

TABLE H______________________________________ ##STR159## .lambda..sub.max.No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 Hue (nm)______________________________________1 C.sub.6 H.sub.5 n-C.sub.13 H.sub.27 CN H yellow 4402 C.sub.6 H.sub.5 n-C.sub.13 H.sub.27 CN Cl yellow 4423 C.sub.6 H.sub.5 i-C.sub.8 H.sub.17 CN Cl yellow 4424 C.sub.6 H.sub.5 i-C.sub.8 H.sub.17 CN OCH.sub.3 yellow 449 ##STR160## i-C.sub.8 H.sub.17 CN H yellow 4416 C.sub.3 H.sub.7 i-C.sub.8 H.sub.17 CN H yellow 4407 C.sub.3 H.sub.7 i-C.sub.8 H.sub.17 CN Cl yellow 4428 CH.sub.3 n-C.sub.13 H.sub.27 CONH.sub.2 H yellow 425.59 CH.sub.3 n-C.sub.13 H.sub.27 CONH.sub.2 Cl yellow 42710 CH.sub.3 n-C.sub.12 H.sub.25 COCH.sub.3 Cl yellow 427.511 CH.sub.3 n-C.sub.12 H.sub.25 COCH.sub.3 H yellow 427.512 ##STR161## n-C.sub.4 H.sub.9 CONH.sub.2 H yellow 42613 C.sub.5 H.sub.11 i-C.sub.8 H.sub.17 CONH.sub.2 H yellow 426______________________________________

EXAMPLE 6

21 parts of the compound of the formula ##STR162## are stirred thoroughly overnight with 50 parts of a 30% strength hydrochloric acid and 1 part of a dispersant which is effective under acidic conditions. The mixture is then cooled to 0.degree.-5.degree. C., and 32-34 parts of a 23% strength sodium nitrite solution are run in under the surface of the suspension in the course of about 20-30 minutes, the temperature being kept at 0.degree.-5.degree. C. during this procedure by the addition of ice. The diazotization mixture is stirred for a further 2-3 hours at from 0.degree. to 5.degree. C., after which about 150 parts of ice water are added, nitrite is destroyed in a conventional manner and the pH of the diazotization mixture is brought to 0.5-1.0 with a little sodium formate. A solution comprising 23.6 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one, 300 parts by volume of water and 12 parts of 50% strength sodium hydroxide solution is then run in. Coupling is complete after a few minutes. The precipitated dye is filtered off under suction, washed with water and dried, these steps being carried out in a conventional manner. 45 parts of a yellow powder of the formula ##STR163## are obtained. The product dissolves in dimethylformamide to give a yellow solution, and dyes polyester fabric in very lightfast deep yellow hues.

EXAMPLE 7

24.5 parts of the diazo component of the formula ##STR164## are diazotized with 33 parts of a 44% strength nitrosylsulfuric acid by a procedure similar to that described in Example 1, the mixture is poured onto ice and water and then stirred until the reaction is complete, and a solution of 23.6 parts of 1-n-hexyl-2-hydroxy-3-cyano-4-methylpyrid-6-one in 250 parts of water and 18 parts of 50% strength sodium hydroxide solution, as well as 1 part of a dispersant (based on an ethylene oxide polymer), are added.

When coupling is complete, the mixture is worked up in a conventional manner to give 48.0 parts of the dye of the formula ##STR165## in the form of a yellow powder. This product dissolves in dimethylformamide to give a yellow solution and gives, on polyester fabric, dyeings having good fastness properties.

EXAMPLE 8

26.5 parts of the diazo component of the formula ##STR166## are diazotized with 34 parts of nitrosylsulfuric acid by a procedure similar to that described in Example 1.

The diazonium salt solution is poured onto ice and stirred to complete the reaction, and 1 part of a dispersant which is effective under acidic conditions is added. Excess nitrous acid is destroyed, after which a solution of 26.4 parts of the coupling component 1-(2-ethylhexyl)-2-hydroxy-3-cyano-4-methylpyrid-6-one in 150 parts by volume of dimethylformamide, 0.5 part of a dispersant, 15 parts of 50% strength sodium hydroxide solution and 30 parts of water are run in, while stirring very thoroughly. Stirring is continued for 1-2 hours, after which the pH of the coupling solution is increased to 6-7.5 by the addition of sodium hydroxide solution.

The product is filtered off under suction, washed with water and dried, these steps being carried out in a conventional manner, and 53 parts of the dye of the formula ##STR167## are obtained in the form of a yellow powder. This product dissolves in dimethylformamide to give a yellow solution, and dyes polyester fabric in very lightfast deep hues.

EXAMPLE 9

Using the roller printing method, a cotton fabric is printed with a printing paste which consists of 15 parts of the dye of the formula ##STR168## 110 parts of polyethylene oxide having a molecular weight of 350, 30 parts of oleic acid diethanolamide and 845 parts of a 10% strength alginate thickener. The print is dried at 100.degree. C., and is then fixed by treating it with hot air at 195.degree. C. for 1 minute. Finishing is carried out and a fast, yellow print on a white ground is obtained.

EXAMPLE 10

On a screen printing machine, a polyester/cellulose blend (weight ratio 67:35) is printed with a mixture which consists of 30 parts of the dye of the formula ##STR169## 100 parts of the reaction product of 3 moles of polyethylene oxide of molecular weight 300 with 1 mole of boric acid, 30 parts of oleic acid diethanolamide and 840 parts of a 3% strength alginate thickener. The print is dried at 110.degree. C., and is then treated with steam at 185.degree. C. for 5 minutes. It is finished and a fast, yellow print on a white ground is obtained.

EXAMPLE 11

Using a padding machine, a cotton fabric is padded with a solution which contains 20 parts of the dye of the ##STR170## 300 parts of a 3% strength alginate thickener, 550 parts of water and 130 parts of polyethylene oxide having a molecular weight of 300. The wet pick-up of the fabric should be 80%. The fabric is dried at 100.degree. C., and the dye is fixed by treatment with steam at 190.degree. C. for 5 minutes. The fabric is then rinsed with cold water, and washed at 90.degree. C. in a bath containing 3 parts of the condensation product of a long-chain alcohol with ethylene oxide in 997 parts of water.

A yellow dyeing is obtained.

Instead of a cotton fabric, it is also possible to pad a polyester/cotton blend (weight ratio 67:33) with the solution described. In the resulting yellow dyeing, the two phases are of the same hue. The treatment with steam can also be replaced by fixing with hot air at 195.degree. C. for 2 minutes.

Claims

1. A compound of the formula ##STR171## wherein R is C.sub.3 -C.sub.17 -alkyl, or phenoxymethyl, and

R.sup.2 is hydrogen, C.sub.1 -C.sub.6 -alkyl or allyl, wherein R.sup.2 is not hydrogen if R is phenoxymethyl.

2. The compound of claim 1, wherein the oxadiazolyl radical is in the m-position.